My career mistakes and missteps

Today marks 3 months in my new job! And I still love it so I want to take a moment to celebrate. I've been looking back over my winding, sometimes seemingly aimless, career journey since graduating from college in 2012. [Almost A DECADE ago. Insanity.] I've been a personal trainer and group exercise instructor, the assistant manager of a corporate gym in a government building, a glorified personal assistant with the title of marketing manager, and held various roles in start-ups spanning sales and account management. Before last summer when everything changed, I'd worked at the local lululemon for over a year. It was a "temporary job to reground" after a lot of job turmoil following my move to NYC and then I'd just stayed. I don't like to silver line, but without a doubt, the impetus to leave a job I didn't like was the best thing that came out of 2020. 

I say this from a place of hindsight, with 20/20 (no pun intended) vision. But even on day one of discovering the affair, I wrote "find a new job" in my laundry list of journaling that filled pages and pages. [It's one of the least violent things I wrote, as it turns out.] When the worst happens, some things become exceedingly clear. And for me, the connection between my prolonged lowered self-worth and my job was a link that looked like crystal. So I took a month of unpaid leave before pulling the trigger and leaving. I got back on LinkedIn and AngelList (LinkedIn for start-ups), polished up my resumé, and began applying for jobs after 6 months of a pandemic. It was really scary. And worth it. I had some super shitty interviews, including one that included taking the G train to Williamsburg and walking almost a mile to Bushwick in loafers not meant for long walks. And then the company turned out to be a joke - like Gen Z'ers who may have been running an MLM acting like they were job creators. Ugh. And interviewing for my current position took two months which was nerve-wracking at a time when my nerves were frayed to the max. But I can confidently say, now on the other side + 90 days, that I made the right decision. And while I don't think I'll ever say that I'm grateful for the infidelity (I've downloaded Esther Perel's book but I'm not ready to even read it yet), I'm so grateful for the push to move past my fear of failure that brought me to my new job. 

I've heard that regrets are only valuable if you learn from them. So here are my top career regrets and associated learnings. I hope that these can be helpful if you are early in your career, contemplating a career change, or just feeling stuck in any aspect of life. Fear is a powerful glue that can hold you back even when you know you are destined for better things. 

  • I regret not sticking up for myself and advocating for myself early in my career. Learning = speak up. Take a beat and speak from a place of reflection, rather than reaction. Tackling issues "in the moment" is overrated. You deserve to sleep on a decision and come back to an important conversation the next day. Another learning = stop thinking of them as "difficult conversations" as that can be a self-fulfilling prophecy. It's an important conversation focused on facts rather than feelings. Full stop. 
  • I regret seeing myself with a really narrow vision, thinking that I had to stay in my degree field of Kinesiology or otherwise work retail. That wasn't true at all. Learning = in the words of Ross Gellar, "PIVOT!". Assess your transferrable skills, apply for a job where you fit MOST of the job description (it's ok if you don't fit all of it, I've also learned), and prepare like crazy for your interview(s). 
  • I regret staying in a job that had turned toxic out of fear. I'd regretted leaving Territory Foods when I did and that previous regret held me in place at lulu despite a change in management that left me feeling unhappy, a return to work in the pandemic that left me feeling unsupported, and the accumulation of a year of little aspects of a job that I knew wasn't right for me. Learning = every situation and circumstance is different. Did I leave Territory too soon? I think I did, yes. Did I leave lululemon too late? It wasn't too late in the sense that I ended up applying for the right job at the right time in the fall AND I think I should've started applying to new jobs after a few months at lululemon, which had been my original plan. Live and learn. 
At this time last year, I never would've written something about work. I hated talking about work, thinking about work - it all filled me with shame. Now I can truly say I love my job, the people I work with, and even my day-to-day tasks of emails, spreadsheets, and slides. It feels like one of the constants right now in a life that feels tenuous and ever-evolving. As I said above, every situation and circumstance is different. So your situation and circumstance of feeling stuck is inevitably different from mine. But I urge you to speak up; to pivot; to take the risk. 

Life is too short to feel stuck. 

Comments